ORGO WEEK 2 Practice PDF

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practice for orgo quiz 1 and 2...

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UML Organic Chemistry I University of Massachusetts Lowell FA19 Organic Chemistry I Exam-1 October 2, 2019

Name:

UML ID #:

Instructions: Please read each question carefully and answer it completely and clearly.

Problem 1 2 3 4 5

Points 39 38 42 22 32

Score

UML Organic Chemistry I 1a) Provide the complete IUPAC name for each of the following compounds. Configuration of chiral carbons are not required.

i)

H3C

CH3

H

iii)

ii)

H H

OH

iv)

v)

H Cl H H

H CH2CH2CH2CH3

1b) Provide the correct structure for each IUPAC name given. i) cis-1,3 dimethylcyclohexane

iii) 1,4-diiodobutane

ii) butylcyclohexane

iv) 1-bromo-3,5-diethylcyclohexane

1c) Study the molecule given then draw both chair conformers of the molecule in the space provided. CH3 HO

OH

HO

NH2 OH

UML Organic Chemistry I 2a) Convert the following Newman projection to a wedge and dash representation.

Cl H H2N

Br OH CH3

wedge and dash

2b) Convert the wedge and dash structure to Newman projections from each of the indicated perspective and place your answer in the space provided.

O

Cl

Br

2c) Provide the structures and IUPAC names of four constitutional isomers with molecular formula C9H17Br. i) ii)

IUPAC name

IUPAC name

iv)

iii)

IUPAC name

IUPAC name

UML Organic Chemistry I 3a) Draw a Newman projection of the molecule below along the C2-C3 bond using the perspective given then perform a complete conformational analysis of the molecule by rotating the back carbon clockwise in 60° increments until a complete revolution is obtained. Label the conformers A-F

OH 2

3

3b) Analyze the energy of all the conformers then draw a relative energy diagram to illustrate how the energy of the molecule changes on rotation.

3c) Convert the following condensed formulas to bond-line structures i) CH3CH2OCOCH2COCl ii) HO2CC6H4CHO (molecule has aromatic ring, aldehyde and carboxylic acid.

UML Organic Chemistry I 4) Write the resonance structure that would result from moving the electrons in the way indicated by the curved arrows.

O

H 2N

4b) Study the structure of molecule (1), shown below and answer the questions that follow. Molecule 1 OH

B O

N N NH

D

N H

Atom

Hybridization

Shape

A B C D

A C

4c) Provide the orbitals used (hybridized or unhybridized) to form each of the indicated bonds. (eg. Csp2-Hs, Cp-Cp, etc.).

A

C A D sigma bond

O

H

B

H O C B D

UML Organic Chemistry I 5) Determine the relationship between the following pairs of molecules. The molecules are either identical, constitutional isomers, conformers of the same molecule or not related to each other. Cl

Cl

e)

a)

Cl b)

Cl

H

f)

H

Br

Cl

c)

Br OH

g)

Cl

Br

Br

OH

d)

h)

O

O

5i) Use curved arrows on each structure to show electron flow to obtain a resonance form that is more stable than the indicated molecule. Be sure to include all lone pairs and formal charges on the molecule.

O

5j) Draw constitutional bond-line isomers of compounds consistent with the following molecular formulas and functional group requirements a) Amine with formula C5H11NO b) Carboxylic acid with formula C4H7O2Cl

END OF EXAM...